52086-32-5Relevant academic research and scientific papers
Enantioselective Radical Ring-Opening Cyanation of Oxime Esters by Dual Photoredox and Copper Catalysis
Chen, Jun,Wang, Peng-Zi,Lu, Bin,Liang, Dong,Yu, Xiao-Ye,Xiao, Wen-Jing,Chen, Jia-Rong
supporting information, p. 9763 - 9768 (2019/11/29)
Catalytic enantioselective chemical reactions involving highly reactive radical species remain largely unexplored. We report herein for the first time a novel enantioselective radical ring-opening cyanation of redox-active oxime esters by dual photoreodox
Photoinduced C—C Bond Cleavage and Oxidation of Cycloketoxime Esters
Zhao, Binlin,Tan, Hui,Chen, Cheng,Jiao, Ning,Shi, Zhuangzhi
supporting information, p. 995 - 999 (2018/09/25)
A novel structural reorganization of cycloketoxime esters beyond the traditional Beckmann rearrangement process has been established to build cyano-containing ketones in the presence of photocatalyst. This novel transformation is remarkable with selective C—C bond cleavage and an oxidation process enabled by DMSO used as the solvent, oxidant, and oxygen source avoiding acid, base and toxic cyanide salts as the cyano source. Further applications in late-stage modification of complex and chiral molecules have also been reported.
Practical Direct α-Arylation of Cyclopentanones by Palladium/Enamine Cooperative Catalysis
Xu, Yan,Su, Tianshun,Huang, Zhongxing,Dong, Guangbin
supporting information, p. 2559 - 2563 (2016/02/18)
Direct arylation of cyclopentanones has been a long-standing challenge because of competitive self-aldol condensation and multiple arylations. Reported herein is a direct mono-α-C-H arylation of cyclopentanones with aryl bromides which is enabled by palla
The identification of 7-[(R)-2-((1S,2S)-2-benzyloxycyclopentylamino)-1- hydroxyethyl]-4-hydroxybenzothiazolone as an inhaled long-acting β2-adrenoceptor agonist
Arnold, Nicola,Beattie, David,Bradley, Michelle,Brearley, Andrew,Brown, Lyndon,Charlton, Steven J.,Fairhurst, Robin A.,Farr, David,Fozard, John,Fullerton, Joe,Gosling, Martin,Hatto, Julia,Janus, Diana,Jones, Darryl,Jordan, Lynne,Lewis, Christine,Maas, Janet,McCarthy, Clive,Mercer, Mark,Oakman, Helen,Press, Neil,Profit, Rachel,Schuerch, Friedrich,Sykes, David,Taylor, Roger J.,Trifilieff, Alexandre,Tuffnell, Andrew
, p. 4341 - 4347 (2014/10/15)
The optimisation of two series of 4-hydroxybenzothiazolone derived β2-adrenoceptor agonists, bearing α-substituted cyclopentyl and β-phenethyl amino-substituents, as inhaled long-acting bronchodilators is described. Analogues were selected for synthesis using a lipophilicity based hypothesis to achieve the targeted rapid onset of action in combination with a long duration of action. The profiling of the two series led to identification of the α-substituted cyclopentyl analogue 2 as the optimal compound with a comparable profile to the inhaled once-daily long-acting β2-adrenoceptor agonist indacaterol. On the basis of these data 2 was promoted as the backup development candidate to indacaterol from the Novartis LABA project.
Highly efficient and enantioselective α-arylation of cycloalkanones by scandium-catalyzed diazoalkane-carbonyl homologation
Rendina, Victor L.,Kaplan, Hilan Z.,Kingsbury, Jason S.
experimental part, p. 686 - 693 (2012/04/04)
Functionalized α-tertiary and -quaternary 2-arylcycloalkanones are rapidly accessed by scandium(III) triflate-catalyzed diazo-alkane-carbonyl homologations. Recent developments have allowed for carbon insertion reactions to be performed with catalyst loadings as low as 0.5 mol% on scales up to 5 mmol. Pairing readily available bis- and tris(oxazoline) based ligands with scandium triflate allows access to arylated medium ring carbocycles with enantioselectivities up to 98:2 er and >98% yield. The formal C-C insertion of aryldiazo-methanes into unsubstituted cycloalkanones provides a single-step solution to the ongoing challenge of α-arylation. Georg Thieme Verlag Stuttgart · New York.
